Office



. A HUE PATENT F1IoEl.

semitones-r nners..esnnelir, ASSIGNOB renzser ifi*cessstm '& cot-onet me -PLAUEL.

am cmm m part of Letters lPatent 115,5 5,245, dated'August 2a, 1894. Application and m 5, 1e94.;s9rm11 .51o,1s2. (Specimens) Patented-iuE ngland arch 9, l898f1io. 5,141; in time June 12,];893L'N0. 201,170; in Belgium January 81, 1894, No- 108,195; in Italy February 3-, -1894=,No.' 44.07 69 in Spain February 17, 1894, Nil- 316,361, and in Austria-Hungaryllarch 5, 1894, No. 44 and 110.299.

To all whom itmay concern:

Be'it knownthat I, ARTHUR WEINBERG, a

. sub'ect of the King of Prussia, and aresident of V rankfort-on-the-Main, Germany, have invented new anduseful Improvements in the Production of New Black Azo Coloring-Mat .ters, of which the following is a specification.

, This invention, for which patents have been obtained in Belgium, No. 108,195, dated Janto uary.31, 1894; in Italy, .No. 440/69, dated February. 3, 1894; in SpairnNo. 15,361, dated February 17, 1894;;in AnstriarHungary, N o. and N o. 299, datedMarch 5, 1894; in Great BritainfNo. 5,141, da'ted March '9, 1893, and i n.France, certificate of addition, dated June 12, 1893, brevet No.-201,770, relates to the'production of new black az'o-coloring matters,

I whichderive from diamidodiphenylaniin (leucoindamin), Black azo-dye stuffs have hith- 2'6 -..'erto never been obtained from this base. The

, new 'coloring matters dye cotton direct and ;are the first black azo-compou'nds of thisclass,

which can be fixed on the fiber by'ox'idation.

This characteristic 1 property is the consez 5 quence of the presence of the indamiue group in the molecule, I

- The general process of producing the new -.dye-stuffs consists in treating diamidodiphonylamin' with nitrous acid, allowing the tetgoma'zocolnpound to react upon one molecule of gemma'amidonaphtolsulpho acid whichis described -in the United States Patent, No.

45, 645, grantedJune 23, 1891, and combining the th us produced intermediate compound 5 directly orindirectly with meta-diamines such as meta phenylenediamine. Iii practically carryingout my invention I proceed forinstance asfollows: Editmplc I.,T'v'enty kilosdiatnidodiphonylamin are dissolybd inwater with sixty kilos of hydrochloric acid; to the cooled solution fourteen 'kilos of nitrite of soda, are slowly added, the solution of the'tetrazo compound is made alkaline by addition of carbonate of 45 soda. The shade of the solution turns to dark red. It is rapidly mixed with a solution of twenty-four kilos of' gamma amidonaphtolsulfoacidi. A black: precipitate of the inter- 1 "mediate compound is formed. Then a solution of twelve kilos meta pheuylenediamin is added."v After standing about twelife hours, the formation of the dye stulE isicoinpleted'. It' separates from the solution. It is filtered OE and dried.

Example II. The intermediate compound,- produced from twentykilos of diamidodiphe nylamin and twenty-four kilos of-gammaamidonaphtolsulfo' acid is prepared as described in the first example; Then the solution is acidulated with hydrdchloricacidand .6 o seven kilos of nitrite 'ofsoda areladded. As

soon as this second dia notation'iscompleted,

the solution is introduced into-an {alkaline solution of twenty-fijpr kilos at inetag-pheny1enediamin.\ .Aftegstandingjabout.twel've 6 hours the formation-of-the dyestuif. is completed. It separatesfrom tliesolutio'n. It is filtered olf and dried. Emawwle III. The intermediate c'oinpound'fl" produced from twenty kilosof diamidodiphe 7o nylamin and twenty-four 'kilos'of gamma.

amidonaphtolsulfo-acid is diazotised with seven kilos ofnitrite of soda, as described in the second example. Then the solution is f" made alkaline'by means of carbonate of soda, 7.5 and a solution of twenty-four kilos of gamma amidonaphtolsulto acid is added. After about half anhour a solution of twelve kilos metaphcuylenediamin is poured into the solution. 7 The formationof the dye-stuff is completed '80 with in twelve hours It-separate's from the solution. It is filtered off and dried."

Example IV. The-intermediate compound produced from twenty kilos of diamidodiphenyla nin and twentyfourki los of gamma- 8 5 amidonaphtolsultoacidisdiazotised and combined with twenty-four kilos of gammaeaml donaphtolsulto acid as described in the third example. Then the solution is acidulated with hydrochloric acid,'and seven kilos 'of nitrite of soda areadded. After about halfan'hour the diaz otised compound is introduced into an alkaline solution of twenty-four kilos of metaphenylenediamiu. The forum.-

tion of the'dye-stuif is completed within about 5 twelve hours. It separates fromthe solution. It is filtered off and dried. The coloring mat} ter'rosulting from each of these methods is a dark black powder, solublein hot water with" a bluish black shade, insoluble in alcohol,

ether or benzene, soluble in concentrated sul' furic acid with a blackish blue shade and is precipitated from this solution by addition of water. By reducing agents the color is destroyed; the characteristical product of the reduction is leuco-indainine, which can easily be recognized by its property of turning green by oxidation. ,The coloring matter dyes unmordantedc ou i; an uikaline bath deep black shades. The dyestulf is completely fixed by a treatment of the dyed fiber with oxidizing agents such as bichromates.

Having now described the nature of my invention and in what manner it can be performed, what I claim as new, and desire to secure by Letters Patent, is-

1. The process forproducing new black azo dyes by treating the diamidodiphenylamin (leuco-indamin) with nitrous acid Eli com 'biniug the thus produced tetrazo compound with gamma amidonaphtolsulfo acid and meta diamins such as meta-phenylenediamin, substantially as described,

2. The new coloring matter deriving ,from

diamidodiphenylamin, gamma amidonaphtolsulfo-acid and meta diamins, which is a black powder, soluble in hot water with bluish black color, insoluble in alcohol, other or bengene,

soluble in concentrated sulfuric acid with blue black color, whichsolution separates a ARTHUR WEINBERG.

, Witnesses:

J EAN GRUND, FRANK H; MASON.

, It is hreby certifid that: in Letters Patent No; 525,245 granted tZB, 18% upon thgapp licamion of Ariiliur weinberg, of l lraaikfort-on-t l g Mqjifi fifiinany OI'ELII K impg,(g yv 'xirmm;i -u I- k "Azo Dyes, errors a2pgarjgqiiifiyigjzofm ion; 'fpllbws'z I ma in; 5119 printed heading; and in the preamble bf the speoificittiibn sffgllqi' vgg i Au s,pma-'Hungai'y, March 5, 1894, No. 44 :md N0. 299; whpg as i' gfSfi l ld g haik bwi d's c rib ed as in A.zostriu,Il-1'arch 5,1892,14/295afidthatiih betgapsPateflhhguld 6; read with these coi'reut-iqus therein that, the same may i msein'tfia Patent 0flme. v V A Signed, countersigned,- and smiled this 11th day of September, A. D. 185?4.

{SEALL JNO. T BEYNQ JDS',

Assistant Secretaqywf the, Interior.

p2 \.t, v ntpreviously obtained for the S3111 invexitio'u is ex x opeouslyfiescrip zk Oountersigned: I

, S. T. FISHER,

' Acting Qo'mmz'ssz'qner of Patents. 

